franklyn
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orphan compound
It seems inconceivable that in the 21 st century a simple molecule could yet
remain to be isolated, but apparently thats what I chanced upon. Try and find
any data or reference to this _ C2Cl5(NH2) penta chloro ethylamine , or perhaps
penta chloro ethanamine , or even 2 - amino - pentachloroethane.
There is only a Pentachloroethane CAS 76-01-7
I was considering the prospect of solvating chloramine H2NCl in tetrachloroethylene
perhaps extracting chloramine H2NCl from aqueous solution by partitioning with
tetrachloroethylene when it occured to me it will likely form the new compound.
H2NCl + CCl2=CCl2 -> C2Cl5(NH2)
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ScienceSquirrel
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Pentachloroethylamine will immediately eliminate two molecules of HCl to form trichloroacetonitrile. that is why it does not exist as a stable
compound.
Some things like this can be formed and characterised by microwave spectroscopy during their fleeting lifetimes
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PHILOU Zrealone
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That's right all those Cl atoms arround makes the H of the NH2 acidic...dus labile and very prone to take Cl(-) away as gaseous HCl
PH Z (PHILOU Zrealone)
"Physic is all what never works; Chemistry is all what stinks and explodes!"-"Life that deadly disease, sexually transmitted."(W.Allen)
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franklyn
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Never can tell where something might lead. If the above is a viable pathway for
trichloroacetonitrile then one could obtain tetraazidomethane C(N3)4 from it
according to -> http://www.scienceonline.org/cgi/content/short/314/5806/1659...
| Quote: | Science 15 December 2006:
Vol. 314. no. 5806, p. 1659
DOI: 10.1126/science.314.5806.1659b
Editors' Choice: Highlights of the recent literature
The relative strength of the triple bond in N2 renders compounds with three or more catenated nitrogen atoms
unstable, often explosively so. Banert et al. have succeeded in the careful preparation and isolation of the nitrogen-
rich dangerously explosive tetraazidomethane C(N3)4, as a colorless liquid at room temperature. The stable, readily
available trichloroacetonitrile molecule proved the most convenient precursor, affording the product after an 18-hour
reaction with sodium azide in acetonitrile solvent. Cycloadducts with three and four equivalents of cyclooctyne could
be isolated in ~5% yield and were characterized crystallographically. Reaction with norbornene, however, yielded
unusual tetrazole derivatives in place of expected 1,3-dipolar cycloaddition adducts. Despite the compound's
instability, the authors acquired clean 13C and 15N nuclear magnetic resonance spectra, as well as vibrational and
mass spectral data, and an estimated boiling point of 165°C. Both Brønsted and Lewis acids accelerated exchange
with free azide. -- JSY
Angew. Chem. Int. Ed. 45, 10.1002/anie.200603960 (2006). |
Post on Tetraazidomethane
http://www.sciencemadness.org/talk/viewthread.php?tid=8271&a...
A closely related thread by Engager _
http://www.sciencemadness.org/talk/viewthread.php?tid=8144&a...
Brauer's page 477 details the preparation of monochloramine.
The production of chloramine is also treated here _
N-substituted hydrazines by anhydrous chloramine.pdf
http://www.sciencemadness.org/talk/viewthread.php?action=att...
Anhydrous chloramine produced in the liquid phase
http://stinet.dtic.mil/oai/oai?verb=getRecord&metadataPr...
Tetrachloroethylene is available as Brakleen ( brake parts cleaner ) from automotive supply.
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16MillionEyes
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What would you classify that type of reaction as?And what solvent would you be using? I'm thinking (depending on the solvent) that the carbons in
tretrachloroethelyne are highly nucleophilic making it an easy target for the amine lone pair to attack (although that chlorine makes a bit bulky),
but I'm also thinking that chlorine atom makes the chloroamine acidic donating its hydrogen to the alkene and doing some type of Sn1 reaction although
far more difficult due to all those electronegative chlorines pulling electron density away from the carbon. This seems like a slippery slope
situation. :/
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ScienceSquirrel
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If you wanted to make trichloroacetonitile you would either;
1) Dehydrate trichloroacetamide with P2O5
2) Chlorinate acetonitrile
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